25428-06-2

Upstream product

• 2759-54-8 N-(4-chlorophenyl)propionamide 
• 103-89-9 4-Methylacetanilide 
• 1438400-35-1 N-(2-acetyl-4-methylphenyl)-4-methylbenzenesulfonamide 
• 180624-14-0 4-methyl-2-[2-(trimethylsilyl)ethynyl]aniline 
• 215589-37-0 2-ethynyl-4-methylaniline 
• 29289-13-2 2-iodo-4-methylaniline 
• 5925-93-9 2-amino-5-methylbenzonitrile 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 917-54-4 methyllithium 
• 106-49-0 p-toluidine 
• 75-05-8 acetonitrile 
• 38818-49-4 5-methyl-2-nitrobenzoyl chloride 
• 21296-92-4 2,3,5-trimethyl-1H-indole 
• 69976-70-1 1-(5-methyl-2-nitrophenyl)-ethanone 

Downstream Products

• 73129-52-9 2'-chloro-5-methylacetophenone 
• 38968-41-1 1-(2-azido-5-methylphenyl)ethan-1-one 
• 326852-80-6 6-(2-acetyl-4-methyl-phenylamino)quinoline-5,8-dione 
• 38968-47-7 N-(2-acetyl-4-methylphenyl)acetamide 
• 38968-48-8 2-Acetylamino-5-acetoxymethyl-acetophenon 
• 23432-40-8 6-methyl-4(1H)-quinolinone 
• 1093116-15-4 N-(2-acetyl-4-methylphenyl)-5'-bromo-2'-methoxybenzamide 
• 1334951-16-4 2-(4-fluorophenyl)-3,5-dimethyl-2H-indazole 
• 1334951-17-5 2-(4-methoxyphenyl)-3,5-dimethyl-2H-indazole 
• 49634-76-6 1-phenyl-1-(2-amino-5-methylphenyl)ethylene 
• 107859-39-2 2-(2-Amino-5-methylphenyl)-propen 

Relevant academic research and scientific papers

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones

The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.

Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks

Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.

Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds

A copper-catalyzed intramolecular cyclization reaction of 2-isocyanoacetophenone derivatives to afford 4-hydroxyquinolines chemoselectively is described. The transformation proceeds through enol tautomerism and a subsequent C-C bond formation. Compared to previous methods, this study provides a new protocol for the construction of 4-hydroxyquinoline compounds from functionalized isocyanides under mild conditions.

Pd-catalyzed regiodivergent synthesis of diverse oxindoles enabled by the versatile heck reaction of carbamoyl chlorides

We report herein a miscellaneous oxindole synthesis bearing an all-carbon quaternary center, enabled by Pd-catalyzed intramolecular cyclization followed by multiple intermolecular Heck reactions of both easily accessible alkene-tethered carbamoyl chlorides and olefins. This protocol obviates the use of prefunctionalized olefinic reagents, exhibits excellent functional group tolerance, and features fascinating reactive versatility.

Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner-Meerwein rearrangement

A catalyst-free intramolecular geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes has been developed. The reaction proceeded through two SET processes with Selectfluor to give a fluorinated cyclopropylcarbinyl cation and a further Wagner-Meerwein rearrangement to generate a cyclobutyl carbocation, which undergoes intramolecular nucleophilic capture by amide to forge fluorinated cyclobuta[b]indoline derivatives. A polycyclic multi-fluorinated byproduct was also formed through a Ritter-type reaction in some cases.

Photo-Fries rearrangement of aryl acetamides: Regioselectivity induced by the aqueous micellar green environment

Photochemical reactions tend to give more than one photoproduct. However, such a reaction can be a powerful synthetic tool when it is possible to conduct it in regioselective conditions yielding a single photoproduct. Water-surfactant solutions as reaction media can be considered as an approach in this context because they show products with different features than those from isotropic solutions. Here we describe results obtained from studying the effect on the prototypical photoreaction, known as the photo-Fries reaction of several substituted acetanilides and α-naphthyl acetamide within surfactant micelles (ionic and non-ionic micelles). This reaction involves homolytic cleavage of a C-N bond to yield a singlet radical pair. The surfactant micelles control the rotational and translational mobility of the radical pair, resulting in noticeable photoproduct selectivity.

Synthesis of bridged benzazocines and benzoxocines by a titanium-catalyzed double-reductive umpolung strategy

A sequence of two titanium(III)-catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo- and benzoxozine building blocks. The first step is a reductive cross-coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn-selectivity for the quinolone functionalization while the anti-diastereomers are obtained as the major products from chromones. With different reaction conditions, the stereochemical outcome can be altered to afford the syn-chromanone products as well. A subsequent reductive ketyl radical cyclization forges the tricyclic title compounds in good yields. A stereochemical model explaining the observed stereoselectivities is provided and the product configurations were unambiguously verified by X-ray analyses and 2D NMR spectroscopic experiments.

Primary amino acid catalyzed asymmetric intramolecular Mannich reaction for the synthesis of 2-aryl-2,3-dihydro-4-quinolones

Primary amino acids are found to be good enantioselective catalysts for the direct asymmetric Mannich reaction between 2-amino acetophenone and aldehydes. The 2-aryl-2,3-dihydro-4-quinoline products are obtained in moderate to good yields and good to high enantioselectivities with 10 mol% of the primary amino acid catalyst under mild reaction conditions.

Br?nsted acid/rhodium(II) cooperative catalytic asymmetric three-component aldol-type reaction for the synthesis of 3-amino oxindoles

Cooperation is key! Chiral Br?nsted acid/rhodium(II) cooperative catalysis enabled an enantioselective three-component aldol-type reaction of 3-diazo oxindoles and anilines with glyoxylates to give highly functionalized and structurally diverse 3-amino oxindoles in high stereoselectivity (>20:1 d.r., 99 % ee; see scheme). Copyright

Ru(ii)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides

Ru(ii)-catalyzed intermolecular ortho-C-H amidation of weakly coordinating aromatic ketones with sulfonyl azides is reported. The developed reaction protocol can be extended to various substituted aromatic ketones to afford a wide range of desired C-N bond formation products in good yields.